Ontology highlight
ABSTRACT:
SUBMITTER: Qian WJ
PROVIDER: S-EPMC4374000 | biostudies-literature | 2015 Apr
REPOSITORIES: biostudies-literature
Organic & biomolecular chemistry 20150305 14
There are few methodologies that yield peptides containing His residues with selective N(τ), N(π)-bis-alkylated imidazole rings. We have found that, under certain conditions, on-resin Mitsunobu coupling of alcohols with peptides having a N(π)-alkylated His residue results in selective and high-yield alkylation of the imidazole N(τ) nitrogen. The reaction requires the presence of a proximal phosphoric, carboxylic or sulfonic acid, and proceeds through an apparent intramolecular mechanism involvin ...[more]